5,6-Dihydroxyindoline

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  • Identifiers

    CAS number
    29539-03-5

    Molecular formula
    C8H9NO2

    SMILES
    C1CNC2=CC(=C(C=C21)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 65.06%
    Phenolic 45.17%
    Burnt 35.81%
    Smoky 27.56%
    Savory 20.44%
    Animal 18.86%
    Spicy 18.81%
    Meaty 18.47%
    Medicinal 17.98%
    Vanilla 16.59%

     

    Flavor
    Bitter 81.45%
    Fruity 24.65%
    Sweet 22.9%
    Odorless 22.36%
    Sweet-like 22.33%
    Mild 20.72%
    Alkaline 20.36%
    Very strong 20.29%
    Indole 19.95%
    Cereal 19.64%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    9.24 (weak base)

    Molecular weight
    151.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    377°C

    Flash point

    • 183.61 ˚C est.

  • Synonyms

    • Indoline-5,6-diol
    • 5,6-Indolinediol
    • 29539-03-5
    • 5,6-Dihydroxyindoline
    • 2,3-dihydro-1H-indole-5,6-diol
    • Leukoaminochrome
    • HH49N58FJ9
    • CHEBI:74683
    • DTXSID80865492
    • RefChem:1072201
    • DTXCID40813893
    • 1H-Indole-5,6-diol, 2,3-dihydro-
    • 56DHInn
    • 2-descarboxy-cyclo-dopa
    • 2,3-Dihydro-5,6-dihydroxyindole
    • 5,6-Dihydroxy-2,3-dihydroindole
    • Leucoaminochrome
    • LEUCODOPAMINOCHROME
    • UNII-HH49N58FJ9
    • SCHEMBL93915
    • SCHEMBL9404859
    • SCHEMBL29358285
    • VGSVNUGKHOVSPK-UHFFFAOYSA-N
    • STR10072
    • MFCD18083762
    • AKOS015915284
    • AC-27802
    • CS-0343102
    • NS00125958
    • C17756
    • G78785
    • Q27144821
    • 29539-03-5

  • Applications

    5,6-Dihydroxyindoline (CAS 29539-03-5) is primarily used as an intermediate in organic synthesis, serving as a building block for heterocyclic compounds and pharmaceutical intermediates; it also provides routes to dyes and pigments through phenolic functionalization; the dihydroxy functionality enables exploration as a starting material for functional polymers and coating formulations, and it is commonly evaluated in research and development for functional heterocycles and polyfunctional materials, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.86
    methanol 8.94
    isopropanol 4.19
    water 2.43
    ethyl acetate 6.79
    n-propanol 3.34
    acetone 12.42
    n-butanol 3.66
    acetonitrile 3.72
    DMF 38.95
    toluene 0.29
    isobutanol 2.88
    1,4-dioxane 11.95
    methyl acetate 6.28
    THF 58.5
    2-butanone 7.02
    n-pentanol 4.4
    sec-butanol 2.89
    n-hexane 0.09
    ethylene glycol 17.32
    NMP 24.69
    cyclohexane 0.05
    DMSO 100.34
    n-butyl acetate 9.32
    n-octanol 9.07
    chloroform 2.9
    n-propyl acetate 6.13
    acetic acid 12.8
    dichloromethane 2.21
    cyclohexanone 9.85
    propylene glycol 8.27
    isopropyl acetate 6.37
    DMAc 55.52
    2-ethoxyethanol 37.23
    isopentanol 6.26
    n-heptane 0.43
    ethyl formate 8.55
    1,2-dichloroethane 2.65
    n-hexanol 12.64
    2-methoxyethanol 53.0
    isobutyl acetate 4.63
    tetrachloromethane 2.06
    n-pentyl acetate 9.08
    transcutol 38.22
    n-heptanol 13.08
    ethylbenzene 0.74
    MIBK 9.82
    2-propoxyethanol 52.23
    tert-butanol 12.13
    MTBE 3.61
    2-butoxyethanol 35.83
    propionic acid 5.83
    o-xylene 0.82
    formic acid 29.06
    diethyl ether 1.39
    m-xylene 1.1
    p-xylene 1.26
    chlorobenzene 1.2
    dimethyl carbonate 9.02
    n-octane 0.38
    formamide 33.86
    cyclopentanone 27.92
    2-pentanone 7.88
    anisole 5.12
    cyclopentyl methyl ether 6.8
    gamma-butyrolactone 32.5
    1-methoxy-2-propanol 38.02
    pyridine 3.24
    3-pentanone 3.56
    furfural 33.81
    n-dodecane 0.49
    diethylene glycol 76.64
    diisopropyl ether 1.47
    tert-amyl alcohol 8.54
    acetylacetone 21.31
    n-hexadecane 0.54
    acetophenone 8.33
    methyl propionate 6.73
    isopentyl acetate 10.48
    trichloroethylene 6.5
    n-nonanol 9.3
    cyclohexanol 2.64
    benzyl alcohol 6.67
    2-ethylhexanol 8.27
    isooctanol 10.93
    dipropyl ether 4.88
    1,2-dichlorobenzene 2.94
    ethyl lactate 11.88
    propylene carbonate 14.07
    n-methylformamide 19.85
    2-pentanol 2.97
    n-pentane 0.05
    1-propoxy-2-propanol 29.11
    1-methoxy-2-propyl acetate 19.01
    2-(2-methoxypropoxy) propanol 27.61
    mesitylene 1.35
    ε-caprolactone 10.32
    p-cymene 2.69
    epichlorohydrin 29.73
    1,1,1-trichloroethane 3.36
    2-aminoethanol 15.31
    morpholine-4-carbaldehyde 39.71
    sulfolane 51.49
    2,2,4-trimethylpentane 0.16
    2-methyltetrahydrofuran 10.57
    n-hexyl acetate 11.28
    isooctane 0.25
    2-(2-butoxyethoxy)ethanol 34.68
    sec-butyl acetate 4.33
    tert-butyl acetate 10.33
    decalin 0.21
    glycerin 39.75
    diglyme 60.36
    acrylic acid 7.63
    isopropyl myristate 6.2
    n-butyric acid 9.25
    acetyl acetate 6.1
    di(2-ethylhexyl) phthalate 8.57
    ethyl propionate 6.07
    nitromethane 35.88
    1,2-diethoxyethane 9.55
    benzonitrile 5.91
    trioctyl phosphate 8.45
    1-bromopropane 0.6
    gamma-valerolactone 39.07
    n-decanol 7.62
    triethyl phosphate 7.14
    4-methyl-2-pentanol 5.07
    propionitrile 2.91
    vinylene carbonate 11.02
    1,1,2-trichlorotrifluoroethane 37.08
    DMS 8.09
    cumene 1.35
    2-octanol 7.7
    2-hexanone 6.83
    octyl acetate 8.26
    limonene 2.73
    1,2-dimethoxyethane 39.01
    ethyl orthosilicate 6.47
    tributyl phosphate 7.32
    diacetone alcohol 26.88
    N,N-dimethylaniline 5.28
    acrylonitrile 6.14
    aniline 1.66
    1,3-propanediol 23.4
    bromobenzene 0.98
    dibromomethane 1.0
    1,1,2,2-tetrachloroethane 7.88
    2-methyl-cyclohexyl acetate 8.43
    tetrabutyl urea 12.02
    diisobutyl methanol 6.47
    2-phenylethanol 13.83
    styrene 0.58
    dioctyl adipate 7.77
    dimethyl sulfate 26.84
    ethyl butyrate 7.73
    methyl lactate 17.49
    butyl lactate 11.97
    diethyl carbonate 5.79
    propanediol butyl ether 21.98
    triethyl orthoformate 7.22
    p-tert-butyltoluene 2.95
    methyl 4-tert-butylbenzoate 17.62
    morpholine 12.51
    tert-butylamine 3.57
    n-dodecanol 6.11
    dimethoxymethane 26.85
    ethylene carbonate 8.65
    cyrene 27.62
    2-ethoxyethyl acetate 13.67
    2-ethylhexyl acetate 7.08
    1,2,4-trichlorobenzene 3.53
    4-methylpyridine 3.05
    dibutyl ether 4.3
    2,6-dimethyl-4-heptanol 6.47
    DEF 10.02
    dimethyl isosorbide 39.28
    tetrachloroethylene 6.89
    eugenol 23.32
    triacetin 11.42
    span 80 18.77
    1,4-butanediol 12.76
    1,1-dichloroethane 1.56
    2-methyl-1-pentanol 5.39
    methyl formate 19.18
    2-methyl-1-butanol 3.89
    n-decane 0.64
    butyronitrile 3.46
    3,7-dimethyl-1-octanol 8.67
    1-chlorooctane 3.09
    1-chlorotetradecane 1.7
    n-nonane 0.51
    undecane 0.54
    tert-butylcyclohexane 0.3
    cyclooctane 0.08
    cyclopentanol 5.91
    tetrahydropyran 2.9
    tert-amyl methyl ether 3.8
    2,5,8-trioxanonane 47.84
    1-hexene 0.32
    2-isopropoxyethanol 22.93
    2,2,2-trifluoroethanol 15.86
    methyl butyrate 8.24

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction